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Tetrahydrofuran → 2-Fluoro-4(2,2,4,4-tetramethyl-chroman-6yl-ethynyl)-benzoic acid methyl ester

HRID 381037
Notes
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Reaction equation

HRID 381037 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[O:9][C:8]([CH3:14])([CH3:13])[CH2:7][C:6]2([CH3:16])[CH3:15])#[CH:2].[CH3:17][O:18][C:19](=[O:28])[C:20]1[CH:25]=[CH:24][C:23](I)=[CH:22][C:21]=1[F:27].C(N(CC)CC)C.O1CCCC1>CCCCCC.[Cu]I.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C(OCC)(=O)C>[CH3:17][O:18][C:19](=[O:28])[C:20]1[CH:25]=[CH:24][C:23]([C:2]#[C:1][C:3]2[CH:4]=[C:5]3[C:10](=[CH:11][CH:12]=2)[O:9][C:8]([CH3:14])([CH3:13])[CH2:7][C:6]3([CH3:16])[CH3:15])=[CH:22][C:21]=1[F:27]
ParticipantsProcedureSources & evidenceReaction notes

Participants

9

Reactant 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 156611382,2,4,4-Tetramethyl-6-ethynylchromanHCID 22568800Methyl 2-fluoro-4-iodobenzoate2×

Product 1

HCID 695488832-Fluoro-4(2,2,4,4-tetramethyl-chroman-6yl-ethynyl)-benzoic acid methyl ester

Reagents, catalysts & solvents 4

HCID 24350
Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)
Catalyst
HCID 178418476HCID 178418476, compoundCatalyst
HCID 8058HexaneSolvent
HCID 8857Ethyl AcetateSolvent

Procedure

Following general procedure F and using 6-ethynyl-2,2,4,4-tetramethylchroman (0.11 g, 0.51 mmol), methyl-2-fluoro-4-iodo-benzoate (Reagent G, 0.14 g, 0.51 mmol), triethyl amine (5 mL), tetrahydrofuran(10 mL), copper(I)iodide(0.030 g, 0.16mmol) and dichlorobis(triphenylphosphine)palladium(II) (0.110 g, 0.16 mmol) followed by flash column chromatography over silica gel (230-400 mesh) using 5-10% ethyl acetate in hexane as the eluent, the title compound was obtained (0.14 g, 79%).

Sources & evidence

ORD record
ord-832514d6ec5e45e1b7244358506ac69b
Source dataset
uspto-grants-2001_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06303785B1

Reaction notes

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On this pageParticipantsProcedureSources & evidenceReaction notes